Journal of Organic Chemistry
Journal of Organic Chemistry
4 years ago

Origin of Stereoselectivity of the Photoinduced Asymmetric Phase-Transfer-Catalyzed Perfluoroalkylation of β-Ketoesters

Origin of Stereoselectivity of the Photoinduced Asymmetric Phase-Transfer-Catalyzed Perfluoroalkylation of β-Ketoesters
Xin Li, Chen Yang, Wei Zhang, Xiao-Song Xue, Yi-He Li, Jin-Pei Cheng
The sources of asymmetric induction in the photoinduced phase-transfer-catalytic perfluoroalkylation of β-ketoesters were interpreted by density functional theory calculations. The calculations indicated that multiple hydrogen-bonding interactions mode rather than π–π stacking interactions model better described the transition structure of the reaction. The quantitative estimation of these noncovalent interactions within the key transition states identified that the O–H···O and specific C–H···O hydrogen bonds play key roles for the stereocontrol.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01130

DOI: 10.1021/acs.joc.7b01130

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